How to cite this paper
Sinenko, V., Los, O., Potikha, L & Brovarets, V. (2024). Functionalized 1,3-thiazoles by combined halogen dance.Current Chemistry Letters, 13(4), 695-706.
Refrences
1 Ramos-Inza S., Aydillo C., Sanmartín C., Plano D. (2020) Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds, in: Nandeshwarappa B. P. (Eds) Heterocycles - Synthesis and Biological Activities. IntechOpen.
2 Alizadeh S. R., Hashemi S. M. (2021) Development and therapeutic potential of 2-aminothiazole derivatives in anticancer drug discovery. Med. Chem. Res., 30 (4) 771-806.
3 Petrou A., Fesatidou M., Geronikaki A. (2021) Thiazole Ring—A Biologically Active Scaffold. Molecules, 26 (11) 3166-3241.
4 Giroud M., Ivkovic J., Martignoni M., Fleuti M., Trapp N., Haap W., Kuglstatter A., Benz J., Kuhn B., Schirmeister T., Diederich F. (2017) Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket. Chem. Med. Chem., 12 (3) 257-270.
5 James D. I., Smith K. M., Jordan A. M., Fairweather E. E., Griffiths L. A., Hamilton N. S., Hitchin J. R., Hutton C. P., Jones S., Kelly P., McGonagle A. E., Small H., Stowell A. J., Tucker J., Waddell I. D., Waszkowycz B., Ogilvie D. J. (2016) First-in-class chemical probes against poly(ADPribose) glycohydrolase (PARG) inhibit DNA repair with differential pharmacology to olaparib. ACS Chem. Biol., 11 (11) 3179-3214.
6 Wei Z., Kozikowski A. P. (2003) A Short and Efficient Synthesis of the Pharmacological Research Tool GW501516 for the Peroxisome Proliferator-Activated Receptor δ. J. Org. Chem., 68 (23) 9116-9118.
7 Brunschweiger A., Koch P., Schlenk M., Rafehi M., Radjainia H., Küppers P., Hinz S., Pineda F., Wiese M., Hockemeyer J., Heer J., Denonne F., Müller C. E. (2016) 8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors. Bioorg. Med. Chem., 24 (21) 5462-5481.
8 Siegrist R., Pozzi D., Jacob G., Torrisi C., Colas K., Braibant B., Mawet J., Pfeifer T., DeKanter R., Roch C., Kessler M., Corminboeuf O., Bezençon O. (2016) Structure-Activity Relationship, Drug Metabolism and Pharmacokinetics Properties Optimization, and in Vivo Studies of New Brain Penetrant Triple T-Type Calcium Channel Blockers. J.Med. Chem., 59 (23) 10661-10675.
9 Kikelj D. and Urleb U. (2002) Product Class 17: Thiazoles, in: Schaumann E. (Eds) Science of Synthesis, Volume 11: Category 2, Hetarenes and Related Ring Systems. Georg Thieme Verlag, Stuttgart, 627-834.
10 Schnürch M., Spina M., Khan A. F., Mihovilovic M. D. and Stanetty P. (2007) Halogen dance reactions – A review. Chem. Soc. Rev., 36 (7) 1046-1057.
11 Stangeland E. L., Sammakia T. (2004) Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624B. J. Org. Chem., 69 (7) 2381-2385.
12 Stanetty P., Schnürch M., Mereiter K., Mihovilovic M. D. (2005) Investigations of the Halogen Dance Reaction on N-Substituted 2-Thiazolamines. J. Org. Chem., 70 (2) 567-574.
13 Schnürch M., Khan A. F., Mihovilovic M. D., and Stanetty P. (2009) Polyarylated Thiazoles via a Combined Halogen Dance – Cross-Coupling Strategy. Eur. J. Org. Chem., 2009 (19) 3228-3236.
14 Pevarello P., Lohmer S., Liberati C., Seneci P., Pesenti C., Prandi A. (2015) Substituted thiazole or oxazole P2X7 receptor antagonists. WO Patent 2015/118019.
15 Bur D., Grisostomi C., Nayler O., Remen L., Vercauteren M., Welford R. (2015) Tricyclic piperidine compounds. WO Patent 2015/75023.
16 Nakano T., Imoto H., Naka K. (2021) Synthesis and Optical Properties of Thiazolo-Chlorin and Porphyrin Skeletons. Org. Lett., 23 (20) 7996-8000.
17 Sinenko V. O., Slivchuk S. R., Bal’on Ya. G., and Brovarets V. S. (2015) Synthesis of 2,5-Di(hydroxyalkyl)-1,3-thiazoles. Russ. J. Gen. Chem., 85 (8) 1855-1861.
18 Meyer E. A., Äänismaa P., Froidevaux S., Keller M., Piali L., Caroff E. (2022) Discovery and in Vivo Evaluation of ACT-660602: A Potent and Selective Antagonist of the Chemokine Receptor CXCR3 for Autoimmune Diseases. J. Med. Chem., 65 (17) 11513-11532.
19 House J. B., Pandya B., Kaplan A. P. (2023) Heterocyclic compounds as triggering receptor expressed on Myeloid cells 2 agonists. WO Patent 2023/86799.
20 Faidallah H. M., Rostom S. A. F., Basaif S. A., Makki M. S. T., Khan K. A. (2013) Synthesis and biological evaluation of some novel urea and thiourea derivatives of isoxazolo[4,5-d]pyridazine and structurally related thiazolo[4,5-d]pyridazine as antimicrobial agents. Arch. Pharm. Res., 36 (11) 1354-1368.
21 McCluskey A., Finn M., Bowman M., Smith R., Keller P. A. (2000) 2,7-Dimethylthiazolo[4,5-d]pyradazine-4-(5H)-thione: A Corticotrophin-Releasing Hormone Type 1 Receptor Agonist. Aust. J. Chem., 53 (11-12) 905-908.
22 Makki M. S. I., Faidallah H. M. (1996) Synthesis and Biological Evaluation of New Fused Thiazolo[4,5-d]Pyridazine Derivatives. J. Chin. Chem. Soc., 43 (5) 433-438.
23 Alluri S., Eisenberg S. M., Grisanti L. A.,Tanner M., Volkow N. D., Kim S. W., Kil K.-E. (2022) Preclinical evaluation of new C-11 labeled benzo-1,4-dioxane PET radiotracers for brain α2C adrenergic receptors. Eur. J. Med. Chem., 243 Art.No: 114764.
24 Reeves C., Romero F. A., Jones C. T., Fenaaux M. (2023) Benzimidazole carboxylic acids as GLP-1R agonists. WO Patent 2023/49518.
25 Enjuro H., Shunsuke M., Keisuke F., Etsu T., Daisuke U., Yasuhiro I. (2022) Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans. J. Antibiot. (Tokyo), 75 (10) 542-551.
26 Li F.-Y., Guo X.-F., Fan Z.-J., Zhang Y.-Q, Zong G.-N., Qian X.-L., Ma L.-Y., Chen L, Zhu Y.-J., Kalinina T., Morzherin Yu.Yu., Belskaya N. P. (2015) Synthesis and biological activities of novel 2-amino-1,3-thiazole-4-carboxylic acid derivatives. Chin. Chem. Lett., 26 (10) 1315-1318.